3-Chloropropiophenone → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 1640717Notes

Reaction equation

HRID 1640717 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:12]([Mg]Br)[CH:13]=[CH2:14]>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:14][CH:13]=[CH2:12]

Participants

4

Reactant 2

HCID 702953-ChloropropiophenoneHCID 178455850HCID 178455850, compound

Product 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-olYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-chloro-1-phenylpropan-1-one (170 g, 1.01 mol) in anhydrous THF (1200 mL) was added allylmagnesium bromide (1.2 L, 1 mol/L) at −78° C. under nitrogen. The formed mixture was stirred for 30 min at −78° C. The reaction was quenched with aqueous NaHCO3 solution. The organic phase was separated, dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography (petroleum ether/EtOAc=100:1) to afford 1-chloro-3-phenylhex-5-en-3-ol (180 g, 86%). 1H NMR (CDCl3): 2.27 (m, 2H), 2.51 (m, 1H), 2.74 (m, 1H), 3.22 (m, 1H), 3.58 (m, 1H), 5.16 (m, 2H), 5.53 (m, 1H), 7.23 (m, 1H), 7.39 (m, 4H).

Workup

  1. customThe reaction was quenched with aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography (petroleum ether/EtOAc=100:1)

Sources & evidence

ORD record
ord-79c9620d6e644e5b9721c1ff95074f17
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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